Issue: October 1989, February 1991, July 1992, August 1993, November 1994, January 1996, September 1997, June 1998, February 1999, July 2001, May 2004, January 2007, January 2011

Blonde bombshell Anderson has been posing for Playboy for three decades. She's also been on more covers for the magazine than any other person, so picking one was a challenge and a privilege. Her tongue-in-cheek January 2007 shoot (pictured above) pretty much epitomizes her relationship with the brand.